EP0356812B1 - Hilfsmittel zur Verwendung mit Pflanzenschutzmitteln - Google Patents
Hilfsmittel zur Verwendung mit Pflanzenschutzmitteln Download PDFInfo
- Publication number
- EP0356812B1 EP0356812B1 EP89115134A EP89115134A EP0356812B1 EP 0356812 B1 EP0356812 B1 EP 0356812B1 EP 89115134 A EP89115134 A EP 89115134A EP 89115134 A EP89115134 A EP 89115134A EP 0356812 B1 EP0356812 B1 EP 0356812B1
- Authority
- EP
- European Patent Office
- Prior art keywords
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- adjuvant
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- component
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000002671 adjuvant Substances 0.000 title claims description 28
- 239000011814 protection agent Substances 0.000 title description 10
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- -1 polyoxyethylene moiety Polymers 0.000 claims description 20
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 13
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- REEXLQXWNOSJKO-UHFFFAOYSA-N 2h-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical compound C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 claims description 6
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- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 3
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- GGWHBJGBERXSLL-NBVRZTHBSA-N chembl113137 Chemical compound C1C(=O)C(C(=N/OCC)/CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-NBVRZTHBSA-N 0.000 description 3
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- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 2
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- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
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- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 2
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 2
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- UJTBQQYWRFOKKK-UHFFFAOYSA-N (3-ethoxy-3-oxopropyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCCC(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 UJTBQQYWRFOKKK-UHFFFAOYSA-N 0.000 description 1
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- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 description 1
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- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 description 1
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- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/06—Protein or carboxylic compound containing
Definitions
- the subject invention relates to adjuvants for crop protection agents which fall into the category of crop oil concentrates. More particularly, the subject invention relates to improved crop oil concentrates which enhance the efficacy of active ingredients, allowing greater or equal weed control while using less active ingredient.
- adjuvants play important roles in the formulation and application of crop protection agents.
- These adjuvants are a diverse group of components with equally diverse functions which may often be determined from their generic names, i.e. "spreaders”, “stickers”, “solubilizers”, “emulsifiers', “flow control agents”, “drift control agents”, and so on.
- crop oil concentrates are the so-called "crop oil concentrates”.
- Crop oil concentrates are often recommended by manufacturers and formulators for inclusion in crop protection agents to increase the efficacy of crop protection agents, especially herbicide formulations.
- Crop oil concentrates are available from a variety of sources, and generally consist of from 75-95 percent by weight of a hydrocarbon oil or solvent with the balance being a surfactant, although in certain cases the surfactant may comprise a majority of the composition, or even all of the composition.
- the hydrocarbons which form a major part of the crop oil concentrate may be derived from mineral (petroleum) or vegetable sources.
- the hydrocarbon component may be predominately paraffinic, or may be aromatic, particularly alkylated aromatic.
- crop oil concentrates enhance as adjuvants the activity of crop protection agents, especially of a spectrum of herbicides over and above the efficacy obtained with other, commercial, adjuvants.
- crop oil concentrates are useful with herbicides containing cyclohexenones, benzothiadiazinone dioxides, diphenyl ethers, quinoline carboxylic acids, (het)aryloxyphenoxypropionic acid derivatives, bipyridilium salts and imidazolinone derivatives, especially with cyclohexenone-type herbicides, increasing the overall effectiveness of formulations of such herbicides.
- the crop oil concentrates of the subject invention comprise a mixture of (a) a first active component which is a low-foaming nonionic surfactant; (b) a second active component which is an anionic surfactant derived from esterification of a polyoxyalkylene nonionic surfactant with a dihydric or trihydric inorganic acid or by carboxylation with an organic acid derivative; and (c) optionally and preferably a third active component which is a lower alkanol ester of a long chain fatty acid, or, when the low-foaming nonionic surfactant is a block surfactant containing oxyethylene and higher oxyalkylene residues, a polyoxyethylated aliphatic alcohol or mixtures of polyoxyethylated aliphatic alcohol and lower alkanol ester.
- a hydrocarbon component is preferably added.
- the low-foaming surfactants (a) are polyoxyalkylene nonionic surfactants initiated with long chain aliphatic alcohols which have little tendency to foam as measured, for example, by the Ross-Miles test.
- the low-foaming surfactant should have a dynamic foam height, measured at 0.1 percent concentration and 50°C, of less than 10 cm, more preferably less than 6 cm, and most preferably 3 cm or less.
- the low-foaming surfactants typically have hydrophile/lipophile (hydrophile/lipophile balance; HLB) values of less than 12, preferably less than 8 and most preferably less than 6.
- the low-foaming surfactants (a) of the subject invention comprise two related types of surfactants or their mixtures. Both types of low foamers are initiated with long chain fatty alcohols having chain lenghts of from 6 to 22, preferably from 10 to 18, and particularly from 13 to 15 carbons in the aliphatic hydrocarbon portion of the molecule.
- One type of low foamer (a) is prepared by oxyethylating the previously described aliphatic alcohols with from 2-6 moles of ethylene oxide, preferably 3-5 moles.
- the second type of low foamer is prepared by oxyalkylating the aliphatic alcohol initiator with both ethylene oxide and a higher alkylene oxide, preferably propylene oxide, butylene oxide, or mixtures thereof.
- the oxyalkylation by the various alkylene oxides may take place substantially sequentially or may take place concurrently, the product having the low-foaming properties previously described.
- the oxyalkylation is sequential and involves the addition of preferably from 2 to 12, more preferably from 2 to 10 moles of ethylene oxide followed by the addition of from 1 to 15, preferably from 1 to 10, moles of higher alkylene oxide.
- butylene oxide is the higher alkylene oxide
- both alkylene oxides are added concurrently to form a low-foaming surfactant, from 2 to 18 moles, preferably 4 to 8 moles, of ethylene oxide are used with from 2 to 10, preferably 3 to 7, moles of higher alkylene oxide.
- the anionic surfactants (b) which are useful in the practice of the subject invention are preferably the partial sulfate and phosphate esters of polyoxyalkylene ethers. These partial esters are prepared by methods well known to those skilled in the art, for example by reacting one of the well known and commercially available monohydric polyoxyalkylene ethers with sulfuric acid or phosphoric acid or their chemical equivalents.
- the sulfate esters so obtained consist predominately of the half ester (monoester) while the phosphate esters generally contain both mono- and di-esters.
- carboxylate surfactants are also useful.
- the methods of preparation of such surfactants are well known to those skilled in the art.
- the sulfate esters may be prepared, for example, by reacting a suitable monofunctional polyoxyalkylene ether with sulfuric acid or its chemical equivalent, preferably sulfamic acid or sulfur trioxide.
- the phosphate esters may be prepared similarly by reaction of the monofunctional polyoxyalkylene ether with phosphoric acid, diphosphorus pentoxide, polyphosphoric acid, or phosphorus oxytrichloride.
- difunctional polyoxyalkylene ethers may be reacted with the phosphate ester producing reagent to form a surfactant containing an internal polyoxyalkylene component terminated with phosphate ester groups.
- nonionic, monofunctional and difunctional polyoxyalkylene ethers used to prepare the sulfate and phosphate esters are also well known to those skilled in the art, and are available commercially from many sources.
- Preferred nonionic polyoxyalkylene ethers have molecular weights of from 400 to 3000 Daltons, more preferably from 600 to 1200 Daltons, and particularly about 800 Daltons.
- the preferred polyethers are prepared by oxyalkylating a monofunctional or difunctional initiator by known methods.
- Preferred initiators are the alkylphenols such as octyl- and nonylphenol, and the aliphatic alcohols, particularly the latter.
- the preferred aliphatic alcohols have from 6 to 30, more preferably from 10 to 20, and in particular from 12 to 16 carbon atoms in the aliphatic residue.
- alkylene oxides which may be used to prepare the nonionic monofunctional polyoxyalkylene intermediates include ethylene oxide, propylene oxide, and butylene oxide. Tetrahydrofuran may also be useful. Preferred alkylene oxides are ethylene oxide and propylene oxide. When both these oxides are utilized, they may be added simultaneously, in sequence, or in combinations of these modes of addition, the prepare block surfactants. Ethylene oxide may also be used alone to form homopolymeric polyoxyethylene polyethers.
- the carboxylate surfactants are derived from oxyethylated aliphatic alcohols by reaction with chloroacetic acid in the presence of base.
- the preparation is described in the Schick treatise, supra, at pages 388-89.
- the aliphatic alcohol contains from 6 to 30, more preferably from 10 to 20, and particularly from 12 to 16, carbon atoms, and is oxyethylated with from 2 to 10, preferably from 3 to 8, moles of ethylene oxide.
- the lower alkanol ester of the long-chain carboxylic acid (c) may be considered as derived from a lower alkanol having from 1 to 4 carbon atoms, such as methyl alcohol, ethyl alcohol, propyl alcohol, or butyl alcohol, and a long chain carboxylic acid.
- the methyl and ethyl esters are preferred. Most particularly, the methyl esters are utilized.
- the long-chain carboxylic acid preferably contains from 6-22 carbon atoms, more preferably from 14-18 carbon atoms.
- carboxylic acids obtainable from natural sources such as fats and oils, for example lauric, myristic, stearic, linoleic, linolenic, palmitic, and oleic acids. Mixtures of these acids are also useful. Preferred are oleic and palmitic acids and their mixtures. Thus the most preferred alkanol esters are methyl oleate, methyl palmitate, and mixtures of these esters. In the remainder of the specification, such compounds will be referred to as lower alkanol esters.
- the low-foaming nonionic surfactant (a) is not a polyoxyethylated aliphatic alcohol
- all or part of the lower alkanol ester (c) may be replaced by a low to moderate foaming type of surfactant.
- examples are the greater than 3 mole, preferably 4-6 mole, oxyethylated alcohols.
- Such alcohols should contain from 6 to 22 carbon atoms and may be aliphatic, cycloaliphatic, aromatic or alkylaromatic in nature.
- Examples of preferred replacement surfactants are the 4 mole oxyethylates of long-chain aliphatic alcohols such as lauryl alcohol.
- Component (d) may be derived principally from vegetable or petroleum sources.
- the aromatic solvents particularly those containing alkylated aromatics such as the benzenes and naphthalenes.
- Component (d) may also be a paraffinic or aromatic "oil” or solvent derived from mineral sources.
- Such solvents are readily available from a number of sources, for example, the Shellsolve® (alkyl aromatic) solvents available from the Shell Oil Co., Houston, Texas, and the Aromatic® 150 and 200 (mixed aromatic) solvents available from Exxon Corporation.
- Suitable paraffinic hydrocarbons are preferably solvent-refined petroleum oil fractions composed of naphthenic as well as paraffinic hydrocarbons with less than 25 weight percent of aromatics.
- Such hydrocarbon "oils” generally have high flashpoints, i.e. above 200°F, preferably above 300°F. Mixtures of paraffinic and aromatic hydrocarbons may also be used.
- the hydrocarbon component (d) may also contain up to about 30 percent by weight, preferably from 10-30 percent by weight, of a solvent-soluble alcohol, for example n-hexanol or isooctanol, to maintain or enhance the physical properties of the blend.
- a solvent-soluble alcohol for example n-hexanol or isooctanol
- Other solvent-soluble alcohols which are suitable are those which generally contain from 5 to 18 carbon atoms, preferably from 5 to 10 carbon atoms.
- the term "hydrocarbon component" as used herein should be taken as including both aliphatic and aromatic solvents as well as their mixtures, including also the solvent-soluble alcohol component described immediately above. The hydrocarbon component is believed to exert a minor biochemical effect in concert with that of the remaining ingredients, and hence may be considered an active ingredient.
- the composition When utilized as a crop oil concentrate without the hydrocarbon component, the composition generally contains, in percent by weight relative to the total weight of the concentrate, from 20 to 90 percent low-foaming surfactant (a), 4 to 40 percent anionic surfactant (b), and 0 to 30 percent lower alkanol ester (c).
- the composition contains 30 to 80 percent low-foaming surfactant, 4 to 20 percent anionic surfactant, and 2 to 16 percent lower alkanol ester. Most preferably it contains 70 to 80 percent low-foaming surfactant, 5 to 10 percent anionic surfactant, and 4 to 12 percent lower alkanol ester.
- the preferred hydrocarbon component-containing crop oil concentrates generally contain, in percent by weight relative to the total weight of the crop oil concentrate, from 10 to 60 percent of low-foaming surfactant, from 2 to 20 percent anionic surfactant, from 0 to 20 percent lower alkanol ester, and from 70 to 30 percent hydrocarbon component. More preferably, the crop oil concentrate contains from 25 to 45 percent low-foaming surfactant, 2 to 10 percent anionic surfactant, 2 to 8 percent lower alkanol ester, and 60 to 40 percent hydrocarbon component.
- the crop oil concentrate contains from 35 to 40 percent low-foaming surfactant, from 5 to 10 percent anionic surfactant, from 4 to 7 percent lower alkanol ester, and from 80 to 20, preferably 40 to 50, percent hydrocarbon component.
- the hydrocarbon component may optionally contain up to 30 percent, preferably from 10 to 20 percent, and most preferably about 18 percent, of a solvent-soluble alcohol.
- Crop protection agents are compositions (formulations) comprising active ingredients and commonly used inert additives in the form of emulsion concentrates, suspension concentrates (flowables), wettable powders or water-dispersible granules. Depending on the active ingredient, such a composition may also be an aqueous solution. These compositions are usually applied as tankmixes, the compositions being adjusted to a certain use concentration by diluting with water.
- the subject invention crop oil concentrates may also be used in conjunction with a nitrogen source such as urea, ammonium sulfate, ammonium nitrate, ammonium phosphate and the like.
- a nitrogen source such as urea, ammonium sulfate, ammonium nitrate, ammonium phosphate and the like.
- the crop oil concentrates of the subject invention have been found effective with crop protection agents containing active ingredients of diverse chemical structure, for example with herbicides from the classes of cyclohexane-1,3-diones, the benzothiadiazinone dioxides, the diphenyl ethers, quinolinecarboxylic acids, (het)aryloxyphenoxypropionic acid derivatives, including quinoxalinyloxyphenoxy herbicides, bipyridilium salts and imidazolinone derivatives and with plant growth regulators, for example thiadiazuron.
- the crop oil concentrates are especially effective with cyclohexenone-type herbicides.
- cyclohexenone herbicides with which the subject invention crop oil concentrates may be used are well known. Examples of their preparation and use may be found in U.S. patents 3,950,420; 4,011,256; 4,249,937; and 4,666,510.
- cyclohexenones including alloxydim (2-[1(allyloxyamino)-butylidene]-5,5-dimethyl-4-methoxycarbonyl-cyclohexane-1,3-dione and its sodium salt), sethoxydim (2-[1-ethoxyamino)-butylidene]-5-(2-ethylthio-propyl)-cyclohexane-1,3-dione), cycloxydim (2-[1-ethoxyamino)-butylidene]-5-(3-thianyl)-cyclohexane-1,3-dione), clethodim (2-[1-(3-chloro-2-propenyl-oxyimino)-propyl]-5-(2-ethylthio-propyl)-cyclohexane-1,3-dione), and cloproxydim (2-[1-[3-chloro-2-propen
- a representative of benzothiadiazinone dioxides is bentazon (3-(1-methylethyl-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxides; U.S. patent 3,708,277).
- diphenyl ether herbicides and their analogues are likewise well known. These herbicides are described, for example, in chapter 14 of Herbicides, P.C. Kearney et al., published by Marcel Dekker, Inc., New York 1976.
- acifluorfen (5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoate sodium salt), bifenox (5-(2,4-dichlorophenoxy)-2-nitro-benzoic acid methyl ester), fluoroglycofen (5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoic acid (2-ethoxycarbonyl-ethyl)-ester), lactofen (5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoic acid (1-ethoxycarbonyl-ethyl)ester) and fomesafen (5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-N-methanesulfonyl-benzamide.
- quinolinecarboxylic acids examples include quinclorac (3,7-dichloro-8-quinoline-carboxylic acid; U.S. patent 4,497,651) and quinmerac (3-methyl-7-chloro-8-quinoline-carboxylic acid; U.S. patent 4,715,889).
- Examples of (het)aryloxyphenoxypropionic acid derivatives are diclofopmethyl (methyl-2-[4-(2,4-dichloro-phenoxy)-phenoxy]-propionate), fluazifop (butyl-2-[4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy]-propionate, haloxyfop (methyl-2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)-phenoxy]-propionate, quinofop-ethyl (ethyl-2-[4-(6-chloro-2-quinoxanyloxy)-phenoxy]-propionate, fenoxaprop-ethyl (ethyl-2-[4-(6-chloro-2-benzoxazolyloxy)-phenoxy]-propionate).
- bipyridilium salts are diquat (1,1′-ethylene-2,2′-bipyridilium dibromide), paraquat (1,1′-dimethyl-4,4′-bipyridilium dichloride) and morfamquat (1,1′-bis(3,5-dimethyl-morpholino-carbonyl methyl)-4,4′-bipyridilium dichloride).
- imidazolinone derivatives are imazaquin (2-[4,5-dihydro-4-methyl-4-(1-methyl-ethyl)-5-oxo-1H-imidazol-2-yl]-3-pyridine-carboxylic acid) and imazethapyr (2-[4,5-dihydro-4-methyl-4-(1-methyl-ethyl)-5-oxo-1H-imidazol-2-yl]-5-ethyl-3-pyridinecarboxylic acid).
- the crop oil concentrates are also useful in promoting the biological activity of various other pesticides such as fungicides, mildewcides, defoliants, and insecticides and plant growth regulators.
- herbicidal and plant growth regulating compositions are tested for their efficacy against a variety of common weeds. In many cases, comparisons are made to similar tankmix compositions but containing other crop oil concentrates.
- the "standard” crop oil concentrate used for comparison purposes is "Booster Plus E", a product of Agway Corporation. This product has been widely used in herbicide applications and appears to have consistent formulation and product quality. In the examples, this "Standard" crop oil concentrate is labeled "OC”.
- the numerical value in the tables represent the percentage of weed control, or percent kill of the various species.
- Adjuvants crop oil concentrates
- Table I Adjuvants (crop oil concentrates) according to the invention were prepared in accordance with the formulations presented in Table I. The ingredients were mixed in the order indicated, all parts being by weight.
- the respective concentrates were added at levels of generally from 0.25 to 5 l/HA to tankmixes containing the active ingredients and agitated to prepare a uniform mixture.
- ABUTH Abutilon theophrasti velvet leaf AVEFA Avena fatua wild oats BRAPP Brachiaria platyphylla broadleaf signal grass BROSE Bromus secalinus cheatgrass CYNDA Cynodon dactylon bermudagrass DATST Datura stramonium jimsonweed DIGSA Digitaria sanguinalis large crabgrass ECHGG Echinochloa crus-galli barnyardgrass HORVX Hordeum vulgare barley (volunteer) IPOSS Ipomoea spp.
- Table II shows the greater effectiveness of the crop oil concentrate of Example 3 when used with a defoliation agent, thidiazuron, in preventing regrowth of cotton.
- Table III summarizes the increased effectiveness of cycloxydim in combating volunteer oats, barley, and wheat in peas (var. "Progress 9").
- Table V summarizes the effectiveness of a crop oil concentrate of the subject invention as compared to the standard concentrate when added to sethoxydim formulations for grass control in peas.
- weed control in soybeans was assessed 29 DAT using sethoxydim at 150 g/HA and various crop oil concentrates at 2 l/HA.
- Table VII indicates the greater effectiveness of the crop oil concentrates of the subject invention in controlling volunteer corn using sethoxydim at a rate of 100 g/HA and various adjuvants at ca. 2 l/HA. TABLE VII Volunteer Corn Control Using 100 g/HA Sethoxydim and Various Adjuvants Adjuvant ZEAMX (30 DAT) ZEAMX (40DAT) OC 40 46 Example 1 75 79 Example 2a 73 65 Example 2 82 89 Example 3 85 86
- Table IX demonstrates the greater control of bermudagrass and johnsongrass by cycloxydim at 200 g/HA in the presence of various adjuvants at 1.0 weight percent in the tankmix.
- Table X demonstrates the increased herbicidal activity of bentazon [3-(1-methylethyl-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide] in broadleaf weed control in soybeans during greenhouse trials. Bentazon was used at a rate of 480 g/HA.
- Table XI demonstrates the greater effectiveness of the subject invention crop oil concentrate as compared to a crop oil concentrate Assist® (an emulsifiable mineral oil). Control of three weed species 41-43 days after treatment averaged from 4-5 locations is presented. The herbicide is sethoxydim used at 150 g/HA.
- Table XII demonstrates the increased effectiveness of the subject invention crop oil concentrates on volunteer barley and wheat 42 DAT.
- the herbicide is sethoxydim used at 200 g/HA.
- the adjuvant is used at 2 l/HA.
- Tables XIII and XIV demonstrate the greater effectiveness of the subject invention crop oil concentrates wich Quinclorac.
- the crop oil concentrate at 4l/HA causes no damage to the crop.
- other commercial crop oil concentrates were both less effective against barnyard grass and exhibited crop damage.
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Claims (11)
- Verwendung von Hilfsmitteln zur Erhöhung der Wirksamkeit von Herbiziden, dadurch gekennzeichnet, daß sie in Gew.-%,a) 20 bis 90 Prozent eines gering schäumenden nichtionogenen Tensids ausgewählt aus der Gruppei) Alkylpolyoxyethylen-polyether, worin die Alkylgruppe 6 bis 22 Kohlenstoffatome enthält und der Polyoxyethylenteil von 2 bis 6 Mol Ethylenoxid abgeleitet ist; sowieii) Alkylpolyoxyalkylen-polyether, worin die Alkylgruppe 6 bis 22 Kohlenstoffatome enthält und der Polyoxyalkylenteil von Ethylenoxid und einem höheren Alkylenoxid abgeleitet ist und worin der Polyether einen HLB-Wert von weniger als 12 aufweist; sowieiii) deren Mischung; sowieb) von 4 bis 40 Prozent eines anionischen Tensids ausgewählt aus der Gruppei) Schwefelsäure- und Phosphorsäure-Teilester sowie Carbonsäureester von monohydroxyfunktionellen Polyoxyalkylenethern; undii) Phosphorsäure-Teilester dihydroxyfunktioneller Polyoxyalkylenether; und gegebenenfallsc) 0 bis 30 Prozent einer dritten Komponente ausgewählt aus der Gruppei) niederer Alkanolester von Carbonsäuren mit 6 bis 22 Kohlenstoffatomen; sowieii) bei Abwesenheit von Komponente a)ii) Alkylpolyoxyethylenpolyether, worin die Alkylgruppe 6 bis 22 Kohlenstoffatome enthält und der Polyoxyethylenteil von 3 bis 8 Mol Ethylenoxid abgeleitet ist, enthalten.
- Verwendung von Hilfsmitteln nach Anspruch 1, dadurch gekennzeichnet, daß sie die Komponenten a), b) und c) in Mengen von 10 bis 90 Gew.-% a), 2 bis 40 Gew.-% b) und 0 bis 30 Gew.-% c) und zusätzlich 80 bis 20 Gew.-% einer Kohlenwasserstoffkomponente mit 100 bis 70 Gew.-%, bezüglich des Gesamtgewichts der Komponente (b), eines Öls des Kohlenwasserstoffs ausgewählt aus der Gruppei) aromatische Kohlenwasserstoffkomponente;ii) aliphatische Kohlenwasserstoffkomponente,iii) deren Mischungen;sowie 0 bis 30 Gew.-% einer lösungsmittellöslichen Alkoholkomponente enthalten.
- Verwendung von Hilfsmitteln nach Anspruch 1, dadurch gekennzeichnet, daß es sich bei dem gering schäumenden Tensid a) um einen Alkylpolyoxyalkylenpolyether mit 2 bis 20 Oxyethylen-Einheiten und 1 bis 15 höheren Polyoxyalkylen-Einheiten ausgewählt aus der Gruppe Polyoxypropylen und Polyoxybutylen handelt und daß jene Alkylgruppe 10 bis 18 Kohlenstoffatome aufweist.
- Herbizide Zusammensetzung mit einem Hilfsmittel nach Anspruch 1 und einem als Herbizid wirkenden Bestandteil ausgewählt aus der Gruppe Cyclohexan-1,3-dione, Benzthiadiazinon-dioxide, Diphenylether, Chinolincarbonsäuren, (Het)Aryloxyphenoxypropionsäurederivate, Bipyridiniumsalze sowie Imidazolinonderivate.
- Herbizide Zusammensetzung mit einem Hilfsmittel nach Anspruch 2 und einem als Herbizid wirkenden Bestandteil ausgewählt aus der Gruppe Cyclohexan-1,3-dione, Benzthiadiazinon-dioxide, Diphenylether, Chinolincarbonsäuren, (Het)Aryloxyphenoxypropionsäurederivate, Bipyridiniumsalze sowie Imidazolinonderivate.
- Herbizide Zusammensetzung nach Anspruch 4, wobei es sich bei dem als Herbizid wirkenden Bestandteil um Cyclohexan-1,3-dion handelt.
- Herbizide Zusammensetzung nach Anspruch 4, wobei es sich bei dem als Herbizid wirkenden Bestandteil um Benzthiadiazinon-dioxid handelt.
- Herbizide Zusammensetzung nach Anspruch 4, wobei es sich bei dem als Herbizid wirkenden Bestandteil um Chinolincarbonsäure handelt.
- Verfahren zur Erhöhung der Wirksamkeit von Herbiziden, dadurch gekennzeichnet, daß man in solche Herbizide das Hilfsmittel des Anspruchs 1 in solchen Mengen einarbeitet, daß sich Bereiche von 0,25 bis 5,0 l/ha ergeben.
- Verfahren zur Erhöhung der Wirksamkeit von Herbiziden, dadurch gekennzeichnet, daß man in solche Herbizide das Hilfsmittel des Anspruchs 2 in solchen Mengen einarbeitet, daß sich Bereiche von 0,25 bis 5,0 l/ha ergeben.
- Zur Verwendung in Tankmischungen geeignete Nachauflauf-Herbizidhilfsmittel, dadurch gekennzeichnet, daß siea) 20 bis 90 Prozent eines gering schäumenden nichtionogenen Tensids ausgewählt aus der Gruppei) Alkylpolyoxyethylen-polyether, worin die Alkylgruppe 6 bis 22 Kohlenstoffatome enthält und der Polyoxyethylenteil von 2 bis 6 Mol Ethylenoxid abgeleitet ist; sowieii) Alkylpolyoxyalkylen-polyether, worin die Alkylgruppe 6 bis 22 Kohlenstoffatome enthält und der Polyoxyalkylenteil von Ethylenoxid und einem höheren Alkylenoxid abgeleitet ist und worin der Polyether einen HLB-Wert von weniger als 12 aufweist; sowieiii) deren Mischung; sowieb) von 4 bis 40 Prozent eines anionischen Tensids ausgewählt aus der Gruppei) Schwefelsäure- und Phosphorsäure-Teilester sowie Carbonsäureester von monohydroxyfunktionellen Polyoxyalkylenethern; undii) Phosphorsäure-Teilester dihydroxyfunktioneller Polyoxyalkylenether; und gegebenenfallsc) 0 bis 30 Prozent einer dritten Komponente ausgewählt aus der Gruppei) niederer Alkanolester von Carbonsäuren mit 6 bis 22 Kohlenstoffatomen; sowieii) bei Abwesenheit von Komponente a)ii) Alkylpolyoxyethylenpolyether, worin die Alkylgruppe 6 bis 22 Kohlenstoffatome enthält und der Polyoxyethylenteil von 3 bis 8 Mol Ethylenoxid abgeleitet ist, enthalten.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US237609 | 1988-08-26 | ||
| US07/237,609 US4966728A (en) | 1988-08-26 | 1988-08-26 | Adjuvants for use with postemergent herbicides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0356812A2 EP0356812A2 (de) | 1990-03-07 |
| EP0356812A3 EP0356812A3 (de) | 1991-05-15 |
| EP0356812B1 true EP0356812B1 (de) | 1993-08-04 |
Family
ID=22894439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP89115134A Expired - Lifetime EP0356812B1 (de) | 1988-08-26 | 1989-08-17 | Hilfsmittel zur Verwendung mit Pflanzenschutzmitteln |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4966728A (de) |
| EP (1) | EP0356812B1 (de) |
| JP (1) | JP2894733B2 (de) |
| KR (1) | KR0144579B1 (de) |
| AU (1) | AU625194B2 (de) |
| BR (1) | BR8904263A (de) |
| DE (1) | DE68908044T2 (de) |
| DK (1) | DK420189A (de) |
| ES (1) | ES2058422T3 (de) |
| IE (1) | IE63658B1 (de) |
| PH (1) | PH26428A (de) |
| ZA (1) | ZA896487B (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8129312B2 (en) | 2002-04-24 | 2012-03-06 | Basf Se | Use of defined alcohol alkoxylates as adjuvants in the agrotechnical field |
| AU2007236058B2 (en) * | 2006-04-07 | 2012-07-12 | Basf Se | Herbicidal mixture, comprising an imidazolinone herbicide and an adjuvant |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5084087A (en) * | 1989-04-26 | 1992-01-28 | Basf Corporation | Ready to dilute adjuvant-containing postemergent herbicide formulations |
| US5078781A (en) * | 1989-06-30 | 1992-01-07 | Imperial Chemical Industries Plc | Bipyridilium herbicidal compositions |
| USRE37313E1 (en) * | 1990-07-19 | 2001-08-07 | Helena Chemical Company | Homogeneous, essentially nonaqueous adjuvant compositions with buffering capability |
| US5580567A (en) * | 1990-07-19 | 1996-12-03 | Helena Chemical Company | Homogeneous, essentially nonaqueous adjuvant compositions with buffering capability |
| US5741502A (en) * | 1990-07-19 | 1998-04-21 | Helena Chemical Co. | Homogeneous, essentially nonaqueous adjuvant compositions with buffering capability |
| US5178795A (en) * | 1990-07-19 | 1993-01-12 | Helena Chemical Company | Homogeneous, essentially nonaqueous adjuvant compositions with buffering capability |
| US5393791A (en) * | 1990-07-19 | 1995-02-28 | Helena Chemical Company | Homogeneous, essentially nonaqueous adjuvant compositions with buffering capability |
| DE4029304A1 (de) * | 1990-09-15 | 1992-03-19 | Hoechst Ag | Synergistische herbizide mittel |
| AU660918B2 (en) * | 1990-10-17 | 1995-07-13 | Arysta Lifescience Corporation | Method and composition for enhancing uptake and transport of bioactive agents in plants |
| EP0566648B2 (de) | 1991-01-08 | 2001-05-30 | Monsanto Company | Herbizide formulierung |
| NZ241579A (en) * | 1991-03-25 | 1994-04-27 | Becton Dickinson Co | Antimicrobial formulations for treating the skin |
| CA2109541A1 (en) * | 1992-12-04 | 1994-06-05 | Thomas J. Ford | Aromatic oil and process for manufacture |
| AU751940B2 (en) * | 1993-05-05 | 2002-09-05 | Innovative Chemical Services Pty Ltd | Herbicide, crop desiccant and defoliant adjuvants |
| AU686552B3 (en) * | 1993-05-05 | 1998-02-05 | Victorian Chemicals International Pty Ltd | Herbicide, crop desiccant and defoliant adjuvant |
| BR9406529A (pt) * | 1993-05-05 | 1996-01-02 | Victorian Chemical Internation | Adjuvantes de herbicida dessecante de colheita e desfolheante |
| BR9506879A (pt) * | 1994-02-24 | 1997-08-19 | Ici Plc | Composição auxiliar concentrado dispersível e/ou solúvel formulação diluida e processos de tratar vegetação e de trabalhar metais |
| US5612305A (en) * | 1995-01-12 | 1997-03-18 | Huntsman Petrochemical Corporation | Mixed surfactant systems for low foam applications |
| US5686384A (en) * | 1995-03-14 | 1997-11-11 | Zeneca Limited | Compatibility agent and method |
| US6235300B1 (en) | 1999-01-19 | 2001-05-22 | Amway Corporation | Plant protecting adjuvant containing topped or peaked alcohol alkoxylates and conventional alcohol alkoxylates |
| AU772265B2 (en) * | 1999-03-05 | 2004-04-22 | Basf Aktiengesellschaft | Herbicidal mixture containing a 3-heterocyclyl-substituted benzoyl derivative and an adjuvant |
| US6566349B1 (en) | 2000-08-28 | 2003-05-20 | Basf Corporation | Safer organophosphorous compositions |
| US6890889B1 (en) * | 2000-09-08 | 2005-05-10 | Syngenta Crop Protection, Inc. | Mesotrione formulations |
| US6423667B1 (en) | 2001-05-15 | 2002-07-23 | Honeywell International Inc. | Ammonium sulfate suspensions in oils |
| DE10156997A1 (de) * | 2001-11-21 | 2003-08-14 | Basf Ag | Verwendung bestimmter Copolymere als Adjuvans und Mittel für den agrotechnischen Bereich |
| US9072294B2 (en) | 2006-02-15 | 2015-07-07 | Cognis Ip Management Gmbh | Emulsifier system and pesticidal formulations containing the emulsifier system |
| GB0907003D0 (en) * | 2009-04-23 | 2009-06-03 | Syngenta Ltd | Formulation |
| EP2305030A1 (de) | 2009-09-14 | 2011-04-06 | Bayer CropScience AG | Alkylpolypropylenglycolpolyethylenglycol enthaltende agrochemische Zusammensetzungen |
| ES2534745T3 (es) * | 2010-09-14 | 2015-04-28 | Basf Se | Composición que contiene un insecticida de piripiropeno y un adyuvante |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3990884A (en) * | 1969-10-23 | 1976-11-09 | Fisons Limited | Herbicidal Composition Comprising 4-chloro-2-butynyl m-chlorocarbanilate |
| US3997322A (en) * | 1970-09-09 | 1976-12-14 | Sun Oil Company Of Pennsylvania | Herbicide carrier oil composition |
| US4174960A (en) * | 1977-02-09 | 1979-11-20 | Lilly Industries Limited | Pesticidal formulation |
| US4182621A (en) * | 1978-02-01 | 1980-01-08 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Composition for inhibiting the growth of plants |
| CA1120745A (en) * | 1980-03-17 | 1982-03-30 | F. Nelson Keeney | Flowable 2-chloro-n-isopropylacetanilide |
| DE3033335A1 (de) * | 1980-09-04 | 1982-04-22 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Verfahren zur herstellung einer lagerstabilen, konzentrierten emulsion von herbizid wirkenden phenoxyalkancarbonsaeureestern |
| US4557751A (en) * | 1981-03-10 | 1985-12-10 | Minnesota Mining And Manufacturing Company | Compositions containing surfactant and broadleaf foliar herbicide |
| PH20618A (en) * | 1982-01-29 | 1987-03-06 | Ici Australia Ltd | Herbicidal 5-(substituted phenyl)-cyclohexan-1,3-dione derivatives |
| US4642338A (en) * | 1983-09-01 | 1987-02-10 | The Dow Chemical Company | Fluorophenoxyphenoxypropionates and derivatives thereof |
| DE3429437A1 (de) * | 1983-12-08 | 1985-06-20 | Basf Ag, 6700 Ludwigshafen | Cyclohexenonderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| DE3573368D1 (en) * | 1984-04-27 | 1989-11-09 | Ciba Geigy Ag | Herbicidal compositions |
| DE3437238A1 (de) * | 1984-10-11 | 1986-04-17 | Basf Ag, 6700 Ludwigshafen | Neue verbindungen, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| US4840660A (en) * | 1985-12-30 | 1989-06-20 | Rhone Poulenc Nederlands B.V. | Plant growth regulator dispersions |
| DE3614788A1 (de) * | 1986-05-02 | 1987-11-05 | Hoechst Ag | Herbizide emulsionen |
| FR2601259B1 (fr) * | 1986-07-11 | 1990-06-22 | Rhone Poulenc Chimie | Nouvelles compositions tensio-actives a base d'esters phosphoriques leur procede de preparation et leur application a la formulation de matieres actives. |
| GB8624644D0 (en) * | 1986-10-14 | 1986-11-19 | Ici Plc | Herbicidal compositions |
| GB8626246D0 (en) * | 1986-11-03 | 1986-12-03 | Monsanto Europe Sa | Compositions containing glyphosate &c |
| US4834908A (en) * | 1987-10-05 | 1989-05-30 | Basf Corporation | Antagonism defeating crop oil concentrates |
-
1988
- 1988-08-26 US US07/237,609 patent/US4966728A/en not_active Expired - Lifetime
-
1989
- 1989-08-17 EP EP89115134A patent/EP0356812B1/de not_active Expired - Lifetime
- 1989-08-17 ES ES89115134T patent/ES2058422T3/es not_active Expired - Lifetime
- 1989-08-17 DE DE89115134T patent/DE68908044T2/de not_active Expired - Lifetime
- 1989-08-21 PH PH39121A patent/PH26428A/en unknown
- 1989-08-23 JP JP1215144A patent/JP2894733B2/ja not_active Expired - Lifetime
- 1989-08-24 BR BR898904263A patent/BR8904263A/pt unknown
- 1989-08-25 AU AU40236/89A patent/AU625194B2/en not_active Expired
- 1989-08-25 DK DK420189A patent/DK420189A/da not_active Application Discontinuation
- 1989-08-25 ZA ZA896487A patent/ZA896487B/xx unknown
- 1989-08-25 IE IE275289A patent/IE63658B1/en not_active IP Right Cessation
- 1989-08-26 KR KR1019890012275A patent/KR0144579B1/ko not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8129312B2 (en) | 2002-04-24 | 2012-03-06 | Basf Se | Use of defined alcohol alkoxylates as adjuvants in the agrotechnical field |
| US8877681B2 (en) | 2002-04-24 | 2014-11-04 | Basf Se | Use of specific alcohol alkoxylates as an adjuvant for agrotechnical applications |
| AU2007236058B2 (en) * | 2006-04-07 | 2012-07-12 | Basf Se | Herbicidal mixture, comprising an imidazolinone herbicide and an adjuvant |
Also Published As
| Publication number | Publication date |
|---|---|
| DE68908044D1 (de) | 1993-09-09 |
| AU4023689A (en) | 1990-03-01 |
| ZA896487B (en) | 1991-04-24 |
| US4966728A (en) | 1990-10-30 |
| KR0144579B1 (ko) | 1998-07-01 |
| IE892752L (en) | 1990-02-26 |
| DK420189D0 (da) | 1989-08-25 |
| EP0356812A3 (de) | 1991-05-15 |
| PH26428A (en) | 1992-07-15 |
| DE68908044T2 (de) | 1993-11-18 |
| JP2894733B2 (ja) | 1999-05-24 |
| KR900002697A (ko) | 1990-03-23 |
| JPH02152901A (ja) | 1990-06-12 |
| BR8904263A (pt) | 1990-04-10 |
| DK420189A (da) | 1990-02-27 |
| EP0356812A2 (de) | 1990-03-07 |
| AU625194B2 (en) | 1992-07-02 |
| IE63658B1 (en) | 1995-05-31 |
| ES2058422T3 (es) | 1994-11-01 |
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